HCID 67148751, compound → HCID 67148063, compound

HRID 1054005Notes

Reaction equation

HRID 1054005 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][C:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:19][C:18]=1[CH:26]=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=O)C1C=CC=CC=1>CO>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][CH2:26][C:18]1[O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:17]=1[CH2:16][CH:12]1[CH2:13][CH2:14][CH2:15][NH:11]1)[CH3:32]

Participants

3

Reactant 1

HCID 67148751HCID 67148751, compound

Product 1

HCID 67148063HCID 67148063, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture containing 47 (1.0 g, 2.3 mmol) and 10% Pd-on-carbon (˜1 g) in anhydrous MeOH (20 mL) was placed under a hydrogen atmosphere (45 PSI) and shaken using a Parr apparatus for 1 h. The catalyst was removed by filtration and the solids were washed with EtOAc and MeOH. The clarified filtrate was concentrated to afford 634 mg (91%) of 48 as an orange oil which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ7.51-7.49 (m, 1H), 7.38-7.35 (m, 1H), 7.21-7.17 (m, 2H), 4.16-4.09 (m, 2H), 3.68-3.59 (m, 2H), 3.12-3.07 (m, 2H), 2.88-2.73 (m, 4H), 1.84-1.69 (m, 4H), 1.43-1.39 (m, 1H), 1.26-1.20 (m, 3H) ppm.

Workup

  1. customfor 1 h
  2. customThe catalyst was removed by filtration
  3. washthe solids were washed with EtOAc and MeOH
  4. concentrationThe clarified filtrate was concentrated

Sources & evidence

ORD record
ord-c08b0f4b453d4021982cab7766082e07
Source dataset
uspto-grants-2016_07
Patent number
US09394249B2

Reaction notes

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